First off, congratulations. Whether through an app or the unprecedented IRL encounter, you managed to land yourself a first date. You should feel accomplished, considering another person found you a combination of charming, relatable and attractive enough to spend an evening together. Now that you have secured a time and place, all that’s left is figuring out what to wear, right? Wrong. While that may sound easy, in practice it is actually somewhat challenging. A first date is nearly always awkward—you barely know one another—so your outfit is a great icebreaker. That said, there’s a fine line between being “fashionable,” which is a compliment, and a “fashion person,” who is elitist and unapproachable. In order to fall firmly in the former and avoid the latter, some rules are in order. Below, we break down exactly what to wear no matter who you’re meeting or where you plan on meeting them. Whether an expert or a novice, striking the right balance allows you to express yourself without alienating your date—a surefire way to land date number two.

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